Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones

The silyl enol ether derivatives of ketones or esters tethered by a hydrocarbon or ether linkage to the 3-position of a pyridine ring undergo dearomatising nucleophilic attack on the ring once it is activated (as an acylpyridinium species) by the addition of methyl chloroformate. The bicyclic dihydr...

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Detalles Bibliográficos
Autores principales: Brice, Heloise, Clayden, Jonathan, Hamilton, Stuart D
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874404/
https://www.ncbi.nlm.nih.gov/pubmed/20502604
http://dx.doi.org/10.3762/bjoc.6.22
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author Brice, Heloise
Clayden, Jonathan
Hamilton, Stuart D
author_facet Brice, Heloise
Clayden, Jonathan
Hamilton, Stuart D
author_sort Brice, Heloise
collection PubMed
description The silyl enol ether derivatives of ketones or esters tethered by a hydrocarbon or ether linkage to the 3-position of a pyridine ring undergo dearomatising nucleophilic attack on the ring once it is activated (as an acylpyridinium species) by the addition of methyl chloroformate. The bicyclic dihydropyridine products are in some cases unstable, but may be isolated after hydrogenation as fused bicyclic piperidines.
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spelling pubmed-28744042010-05-25 Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones Brice, Heloise Clayden, Jonathan Hamilton, Stuart D Beilstein J Org Chem Full Research Paper The silyl enol ether derivatives of ketones or esters tethered by a hydrocarbon or ether linkage to the 3-position of a pyridine ring undergo dearomatising nucleophilic attack on the ring once it is activated (as an acylpyridinium species) by the addition of methyl chloroformate. The bicyclic dihydropyridine products are in some cases unstable, but may be isolated after hydrogenation as fused bicyclic piperidines. Beilstein-Institut 2010-03-02 /pmc/articles/PMC2874404/ /pubmed/20502604 http://dx.doi.org/10.3762/bjoc.6.22 Text en Copyright © 2010, Brice et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Brice, Heloise
Clayden, Jonathan
Hamilton, Stuart D
Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones
title Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones
title_full Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones
title_fullStr Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones
title_full_unstemmed Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones
title_short Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones
title_sort fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874404/
https://www.ncbi.nlm.nih.gov/pubmed/20502604
http://dx.doi.org/10.3762/bjoc.6.22
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AT claydenjonathan fusedbicyclicpiperidinesanddihydropyridinesbydearomatisingcyclisationoftheenolatesofnicotinylsubstitutedestersandketones
AT hamiltonstuartd fusedbicyclicpiperidinesanddihydropyridinesbydearomatisingcyclisationoftheenolatesofnicotinylsubstitutedestersandketones

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